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Family-friendly holiday rentals in Maitland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Maitland family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Flat in Orlando
4.75 out of 5 average rating, 591 reviews

Luxury condo in Orlando 1 br/1 ba

RabindraRating, 5 stars1 month ago
good place to stay, close to all attractions and MCO airport.
Guest favourite
Apartment in Florida Center
4.81 out of 5 average rating, 164 reviews

INTERNATIONAL dr/UNIVERSAL 2 BEDROOMS KING SUITES

ArlindaRating, 5 stars2 weeks ago
Good location with lots of restaurants in the area. The building feels dated but the apartment is clean and good value. We cooked a couple meals and the kitchen was adequate. The host communicated throughout our stay and friendly. There was adequate parking. We did not check out the amenities.
Top guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 143 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

AnyelisRating, 5 stars3 weeks ago
The house was absolutely gorgeous and was exactly like in the pictures. The hosts were extremely friendly and communicative through our entire stay and even before. It was very clean, had everything one needs during a vacation, and very peaceful. We will be booking again soon!
Superhost
Apartment in Orlando
4.83 out of 5 average rating, 134 reviews

Fantastic 3BR Condo close to OCCC & Epic Universe!

HelenaRating, 5 stars1 week ago
Very comfortable, in a great location - close to amenities and easy for Uber to find. Dennis was super helpful and responded in minutes.
Guest favourite
Apartment in Florida Center
4.9 out of 5 average rating, 125 reviews

The Point Hotel & Suites - 705H Luxury - Pool View

CaitlynRating, 5 stars1 month ago
Enjoyed my stay. We really appreciated the location and the amenities provided in the room. Thank you for the stay!
Superhost
Flat in Davenport
4.77 out of 5 average rating, 237 reviews

Stunning Newly Renovated Condo 10 min to Disney

TakayahRating, 5 stars1 month ago
Great stay for me and my boyfriend. Highly recommended!!
Guest favourite
Apartment in Orlando
4.9 out of 5 average rating, 164 reviews

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

Sarah JaneRating, 5 stars5 months ago
We’ve been staying at one of Daniel’s listings for the past three years, and he never disappoints—not even the place itself! It truly feels like our second home whenever we visit Florida. Daniel is super flexible, especially with early check-ins, which has been a lifesaver with a toddler. He’s always accommodating and responds to messages so quickly. We’re 100% coming back and will continue using Daniel’s Airbnb listings. My daughter calls it “the tower house,” and we all absolutely love it—it’s perfect for families!
Superhost
Townhouse in Kissimmee
4.88 out of 5 average rating, 179 reviews

Elegant 4bdrs lakefront w/private pool

RebeccaRating, 5 stars1 month ago
We had a fantastic stay with friends at this Airbnb! The location was great—close to everything we needed. The rooms were spacious, clean, and beautifully presented. The pool was spotless and perfect for relaxing, and we really appreciated having access to the barbecue, which made our stay even more enjoyable. Simone was an excellent host—so easy to communicate with and provided clear, straightforward instructions for both check-in and check-out. Highly recommend and would definitely stay again!

Family- and pet-friendly home rentals

Guest favourite
Townhouse in Orlando
4.84 out of 5 average rating, 290 reviews

Close to Convention, Epic Universal, Disney, Icon

LachlanRating, 5 stars1 week ago
The stay was great, very clean house and very cozy too. It was a great hangout spot for me and my friends, and it was very easy to get everywhere with ubers always in the area. We didn’t have time to use the amenities at all but it was nice knowing we had access to them. The house was also in really good condition. The only thing I noticed is that most of the doors with locks didn’t lock (bathrooms did though don’t worry). Maybe that was on purpose but it wasn’t an issue just an observation.
Superhost
Townhouse in Kissimmee
4.7 out of 5 average rating, 166 reviews

Cozy Townhouse in Kissimmee, near Orlando!

LakmalRating, 5 stars2 months ago
We stayed for 7 days at this lovely townhouse and had a fantastic time. The location was ideal—just a short drive from Disney and other major attractions. The neighborhood felt safe and quiet, which was great for relaxing after busy days out. The townhouse was clean, spacious, and well-equipped. The kitchen had everything we needed to cook meals, and having a washer and dryer was super convenient. The Wi-Fi worked well, and the air conditioning kept the whole place cool and comfortable. The kids especially loved the community pool.
Top guest favourite
Villa in Kissimmee
4.86 out of 5 average rating, 411 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

ShamayaRating, 5 stars1 week ago
We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !
Superhost
Flat in Orlando
4.89 out of 5 average rating, 248 reviews

Vista Cay Orlando Convention Luxury 3 bed condo

RobertRating, 5 stars1 month ago
Great place no issues at all Jetty allowed us to extend our stay 2 days no problems definitely will return.
Top guest favourite
Townhouse in Kissimmee
4.99 out of 5 average rating, 104 reviews

Family friendly/Pet friendly Orlando paradise

CatherineRating, 5 stars4 days ago
We spent two weeks at Disney parks and this place was an excellent choice for our family of 3. We were close enough to take breaks during the hottest parts of the day. Andrea's place was very clean and comfortable. We appreciated all the amenities provided and clear instructions for check in/out. We would not hesitate to stay here again. Excellent host!!
Guest favourite
Townhouse in Orlando
4.77 out of 5 average rating, 176 reviews

Lake 1BR Villa-near Convention, Universal-Disney!

AmberRating, 5 stars4 weeks ago
We are so grateful to have found this beautiful space. We really enjoyed all of the little thoughtful and cute decor details and the style of the villa. The community was quiet and felt safe. My husband and I also enjoyed the cleanliness of the unit and the comfort of the furniture, especially the beds! We appreciated the extra items, like the blow dryer and the soaps. The quality of the towels and linens were great. The wine was a thoughtful touch, though neither of us drink. The location is phenomenal! We were so close to everything! We were able to explore so much! We offer a special thanks to Kenny and his family for opening this home to us! I definitely recommend staying here whether you are going to Universal or Disney. So much to explore!
Top guest favourite
Home in Sanford
4.95 out of 5 average rating, 190 reviews

Historic Sanford Sunshine Cottage w/ Treetop suite

RachelRating, 5 stars3 months ago
This was a really fun, unique place to stay while we were in town for a family wedding. We particularly enjoyed hanging out on the screened porch upstairs. Sara was really accommodating with an early check-in when we ended up on a very early morning flight, which was SO appreciated. We’d definitely stay again.
Top guest favourite
Villa in Davenport
4.91 out of 5 average rating, 188 reviews

Beautiful villa home near Disney

SarahRating, 5 stars1 month ago
EXCELLENT. My family has been coming in mixed groups for the past 7 years, and this stay has been the best one. Besides being much cleaner than last year's rental (father suffered many flea bites from the couch that was not to have had pets on it), AND being an early check-in despite previous renters leaving issues that were diligently resolved by management/cleaning crew, this house was GORGEOUS. This is not a sterile rental, but someone's home...reflected in the beautiful landscaping [so many things flowering during our stay!], lavish pool set up (kiddy pool, hot tub, and main pool), and abundance of supplies here. We loved that they accommodate large multi-family groups with spacious rooms, a 2nd fridge, [also, the SPICE rack....cooking was so easy with so much on hand], and the supplies available for small children at the house: crib, books, potty chair, high chair, step stool, a double STROLLER, and car seat... and dog-friendly yet clean. THANK YOU, David and Mark!

Family-friendly home rentals with a pool

Guest favourite
Flat in Sorrento
4.93 out of 5 average rating, 342 reviews

Quiet Neighborhood in the Country

YarleneRating, 5 stars1 week ago
The person in charge very attentive and willing to help in whatever is necessary flexible and very accessible entrance. Very clean place, super clean pool and very cosy place. Very quiet neighborhood.
Top guest favourite
Houseboat in Sanford
4.98 out of 5 average rating, 191 reviews

Floating Cottage - Summer/Fall Rates Reduced

MarilynRating, 5 stars1 month ago
We loved feeding the turtles 🐢. You have to check out downtown Sanford, walk the Riverwalk & go to the Central Florida Zoo & Botanical Gardens. Don't forget to try the Jailhouse Restaurant - in a real old jailhouse, great food! She was an amazing host.
Guest favourite
Guest house in Orlando
4.83 out of 5 average rating, 341 reviews

Nice Brand New Studio !!

VanessaRating, 5 stars3 months ago
Cute, cozy place with a pool. Perfect for a couple, close to everything. Hosts were friendly and responsive.
Superhost
Home in Kissimmee
4.89 out of 5 average rating, 182 reviews

Luxurious Private Retreat w/Spa & Saltwater Pool

JessicaRating, 5 stars1 month ago
Carrie thank you so much for hosting our family! This was so much better for our family than a hotel! Our kids never said they were bored! The next time we are in the Orlando area we will book again for sure!
Superhost
Apartment in Kissimmee
4.88 out of 5 average rating, 119 reviews

2-104 Legacy Dunes, Lake View, Heated Pool, Gym

KarolinaRating, 5 stars1 week ago
A very nice place with everything you need for a comfortable stay. We hope to return soon.
Guest favourite
Cottage in Kissimmee
4.93 out of 5 average rating, 405 reviews

Bungalow cottage close to Disney Universal, for 4!

MayaRating, 5 stars1 month ago
A lovely cozy tiny house. All themed parks can be reached in about 30 minutes. Walmart around the corner The house has everything you need. The only thing you might miss is a barbecue. Oh and I looked for scissors in vain. The house is not brand new, which you also see in some places, but it is clean and cozy. We had a lovely time there.
Superhost
Guest suite in Kissimmee
4.83 out of 5 average rating, 590 reviews

Private 2 bedroom w/bathrm in portion of POOL home

JessicaRating, 5 stars5 days ago
This place was so nice for my daughter and I. We were welcomed with open arms and the place was just as described. We met the grounds keeper CC who was a joy to meet. It was quiet and conveniently located. We will definitely stay again.
Superhost
Home in Davenport
4.81 out of 5 average rating, 126 reviews

Mintra’s Villa Pool & Spa

DemetriusRating, 5 stars1 month ago
My girl had a wonderful time her first time in Florida and the place was amazing and felt like home….this a great place and would rent it again…top tier

Quick stats about holiday rentals that are family-friendly in Maitland

  • Total rentals

    50 properties

  • Nightly prices starting at

    $26 SGD before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore